Skip-Level Meetings: Common Pitfalls And How to Avoid Them
Article summary
Skip-level meetings can be powerful, but common interpersonal dynamics and leadership shortcomings can derail them. This article offers a guide to common issues and dynamics that make these meetings ineffective, and tips for how to address them, both for leaders like managers of managers, and employees/skip-level reports.
Takeaways:
Unclear Expectations: Leaders should set clear agendas and goals for skip-level meetings. Skip-level reports/employees should feel comfortable asking for clarification if needed.
Weak Relationships: Understand that low trust is normal. Leaders, show genuine curiosity and follow through on commitments to build trust over time.
Power Imbalance: Be mindful of how the power difference can make participants hesitant. Aim for open, genuine dialogue to counteract this.
Undermining Line Managers: Be careful not to make promises about career development without consulting the employee's direct manager. Always align with the manager afterward.
Feedback Triangulation: If participants bring up concerns about others, guide them toward addressing these concerns with the person directly or their line manager.
Lack of Follow-Through: Actions speak louder than words. Both leaders and employees should follow up with anything they commit to during the meeting.
Cancellations: Leaders, avoid regularly canceling skip-level meetings. This sends a negative message and erodes trust.
Skip-level one-to-ones and other meetings that “skip” a level in your hierarchy can be a great direct communication line between senior leaders and employees who report to middle managers. They can be powerful tools for alignment and building trust. In a previous article, I shared why these meetings matter and a step-by-step guide for making your skip-level meetings successful, with templates for preparing yourself and your skip-level reports to make the most out of your time together.
As a senior leader or middle manager, your skip-level one-to-ones will be much better if you’re conscious of the dynamics that are present in them: Unclear expectations, low trust, power dynamics, unintentionally undermining the line manager, and more can make skip-level meetings awkward and ineffective.
In this article, you’ll find an overview of common interpersonal dynamics that very often occurr in these meetings, based on my own experience in leadership roles, as well as from my coachees and organizational development clients. I’m also sharing concrete tips with you for addressing or handling these dynamics, both for leaders and skip-level reports/employees meeting with them.
Note on terms used: I refer to skip-level one-to-ones as the meeting, as it’s most commonly used (even though group meetings can also work well!), the leader as the person hosting such meetings, and the skip-level report(s) as the person/people participating in it.
Before the meeting
Unclear expectations
Often, leaders feel like they should run such meetings, but aren’t sure how exactly or what to expect from them. Many skip-level reports similarly feel that they can’t decline and should participate, but aren’t clear on what’s expected of them; even worse, they may be afraid to ask out of fear of being perceived as incompetent.
People often just don't understand what a skip-level meeting is and how to use it effectively. Especially more junior folks or people who aren’t familiar with the concept often need help there, or people who work in organizations that have grown fast and where further leadership levels were only introduced over time.
What to do: As the leader running this meeting, set clear expectations beforehand, e.g. by sharing a clear agenda or ideas for what people can ask; this article has a lot of examples and questions you can share.
If you’re the skip-level report asked to attend such a meeting, but didn’t get an agenda, know that it’s okay to ask! Either beforehand or at the start of the meeting, you may e.g. ask, “is there anything you’d like me to prepare?”, “what would you like to get out of the meeting?”, “what do folks typically talk about?”
Weak existing relationship
By its nature, the leader and skip-level report usually don’t have a close relationship; the only exception is often in startups and scaleups as they grow, where the leader and skip-level report may have worked together closely in the past. This typically means there’s low trust. As skip-level meetings are often run at a low frequency (monthly or even more rarely), that’s likely not going to change much.
What to do: As a leader, be mindful that, even if you’re genuinely open to and interested in it, your skip-level report may not be comfortable sharing a lot of feedback or express criticism; it’s an unfortunate part of your job. Over time and through consistent actions, you’ll hopefully be able to build more trust - or get feedback indirectly through someone the employee trusts, like their direct manager.
As the skip-level report, know that it’s okay to be a bit hesitant about what to talk about. You can also ask your teammates about how they’re using these meetings and what they talk about with this leader.
Perceptions play a stronger role
Instead of a strong relationship, perceptions of one another often play a much bigger role in shaping what the leader and skip-level report think of one another: The report may mostly see and hear from the leader in larger group settings like department or domain meetings; the leader may have only heard about the skip-level report’s work anecdotally. These perceptions are often anecdotal and can also lead to skewed impressions that are rarely made explicit (“this leader is a good listener/always cuts people off”, “this skip-level report shipped a great project/caused an incident”) and cognitive biases (halo effect, horn effect).
What to do: As a leader, your instinct (i.e., the sum of your experiences, biases, perceptions, etc.) can be a helpful tool in making decisions quickly or assessing risks. They also have a huge blast radius and disproportionate impact on the people around you, especially at lower levels in your organization. It can be helpful to ask yourself: “What preconceived notions do I have of this person? What is my perception of them?” In addition, in any areas where your biases will play out very directly (performance reviews, calibrations, promotions), make sure there are checks and balances in place to ensure those aren’t impacting decisions.
As the skip-level report, you can use skip-level meetings to understand how your work is perceived at higher levels of the organization. This can be really useful information; here’s more about how to understand and address the perceptions others have of you.
During & after the skip-level meeting
Power dynamics impact the interactions
The setting alone (skipping an organizational level) means that there’s usually a large delta in power between the two people present in the meeting. Especially for the skip-level report, this can mean that they’re much more self-conscious than they’d normally be, and that they may wonder about things like:
How will the leader perceive what I’m saying?
Is anything going to negatively impact how they think about my work/my team/my manager/other people?
Is anything going to reflect negatively on my performance, promotion opportunities,…?
What to do: As a leader, setting clear expectations will go a long way, especially when you already tell your skip-level reports beforehand what they can ask about and what goal you have with these meetings. In addition, you’ll build a lot of trust by being genuinely open to their perspective and being consistent: Following up on your commitments and not regularly cancelling these meetings on a short notice.
As a skip-level report/employee, it’s understandable to wonder how safe it is to especially give critical feedback. As you meet your skip-level manager more often, you should get a better sense of how they handle it.
Unintentionally undermining the line manager’s work/role
What to do: As a leader, don’t make promises on things like development opportunities or career growth without checking with the skip level report’s line manager. You can and should talk about these topics, but either get context from your skip-level report’s manager beforehand or avoid committing to specifics, and give the manager a short summary afterwards. I see this too often: Even vague sentiments like “I really care about your growth”, or “I want to make sure your work is rewarded”, while well-intended, lead to huge disappointment when they’re not followed up by actions.
A simple way to avoid this: When you see skip-level meetings coming up in your calendar, send a quick note to your direct report (i.e., the manager of the skip-level report you’ll be talking to): “Hey, I have a skip-level meeting coming up with $name; is there anything I should be aware of/consider?” It’s a great way to build alignment and speak with “one voice.”
As the skip-level report/employee, it helps to make sure to share everything you bring up to your bosses’ boss with your boss directly as well; if you have a good working relationship with both, it will help make sure you all are on the same page. There may also be situations where you have difficulties working with your manager and need their manager’s advice for how to handle the situation and don’t want to do this (yet).
Triangulating feedback
What to do: As a leader, it may happen that your skip-level reports share feedback in your skip-level meeting about someone else in the company. Whenever this happens, try to understand if they’ve spoken about this with their manager, and, if not, what’s gotten in the way of them doing so. It can also be an opportunity to coach them on how to bring this to their line manager. In any case, unless there are good reasons for this, avoid that this becomes a topic that the line manager isn’t aware of.
Committing to action items you won’t (be able to) follow through on
What to do: For you as a leader, this may be your 5th skip-level meeting for the week; for the person sitting across from you, it may be the only one this quarter. People remember what you commit to, so follow through on it.
As a skip-level report/employee, make sure to follow up on anything you commit to from the meeting. If you’re not hearing back from your manager’s boss about things they promised they’d do within a reasonable time frame, it’s also okay to follow up, or check with your manager about what to do.
Regularly cancelling or moving skip-level meetings
What to do: As a leader and skip-level report/employee, this is not a good look. Especially for leaders, regularly canceling these meetings will send a message that you do not care and don’t honor your commitments. It will undermine a culture of accountability in your organization.
A word of caution for leaders: Don’t rely on skip-level meetings to assess manager performance
A widely-shared notion in management literature is that skip-level meetings are supposed to be a good place for higher-level leaders to check on manager performance (e.g. meeting with your skip-level report to hear about the performance of your direct report, i.e. their manager).
In my experience, that's basically never true:
Most people don't like to talk badly or even critically about their direct manager, let alone in front of that person's boss. In addition, the challenges mentioned above (low trust, impact of perceptions, power dynamics) make this even trickier. This means:
It's still worth doing your best to make skip-level meetings a space where the skip-level report can bring up any concerns they have about their manager’s performance. Just don’t rely exclusively on skip-level meetings to get such feedback.
More effective ways to check on manager/direct reports’ performance are onboarding surveys, regular and well-utilized employee engagement surveys, 360 feedback and other direct reviews, as well as various open feedback channels.
Skip-level meetings offer a unique opportunity to foster open communication and alignment throughout your organization. Navigating the complexities they bring takes awareness and intentional effort. Building strong skip-level relationships won't happen overnight, but it's a worthwhile investment. Don't be discouraged if your first few meetings feel a bit awkward; each one is a step towards greater understanding and a more cohesive team. Remember, consistency and genuine care for your team will foster trust over time. Are you ready to transform your skip-level meetings?
